ORGANIC CHEMISTRY SAPLING ACCESS + ETEX
ORGANIC CHEMISTRY SAPLING ACCESS + ETEX
6th Edition
ISBN: 9781319306977
Author: LOUDON
Publisher: INTER MAC
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Chapter 28, Problem 28.25P
Interpretation Introduction

Interpretation:

When previtamin D2 (which is identical to previtamin D3, p. 1478, except for the R-group) is isolated and irradiated, ergosterol is obtained along with a stereoisomer, lumisterol. The origin of lumisterol is to be explained mechanistically.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 28, Problem 28.25P

Concept introduction:

Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. In phase orbital overlap results in symmetry allowed electrocyclic reactions. Selection rules of electrocyclic reactions are;

No. of electrons Activation mode Stereochemistry of rotation
4n Thermal
Photochemical
Con
Dis
4n + 2 Thermal
Photochemical
Dis
Con

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